CN103044500B - A kind of organic acid preparation and antibacterial applications - Google Patents
A kind of organic acid preparation and antibacterial applications Download PDFInfo
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- CN103044500B CN103044500B CN201210585946.XA CN201210585946A CN103044500B CN 103044500 B CN103044500 B CN 103044500B CN 201210585946 A CN201210585946 A CN 201210585946A CN 103044500 B CN103044500 B CN 103044500B
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- organic acid
- caulis cyatheae
- cyatheae spinulosae
- alcohol
- spinulosae
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- UEBMSFDLNOOUHH-CORZUEPISA-N C[C@@]1(C(C2O)O)OC1C(CO)OC2Oc(ccc(/C=C/C(O)=O)c1)c1OC(C)=O Chemical compound C[C@@]1(C(C2O)O)OC1C(CO)OC2Oc(ccc(/C=C/C(O)=O)c1)c1OC(C)=O UEBMSFDLNOOUHH-CORZUEPISA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses separation obtains from Cyatheaceae Caulis cyatheae spinulosae platymiscium Caulis cyatheae spinulosae (Alsophila spinutosa) a kind of novel organic acid preparation method and the application in antibacterials.With Cyatheaceae Caulis cyatheae spinulosae platymiscium Caulis cyatheae spinulosae stem for raw material, through alcohol extraction, it is concentrated into after without alcohol, extract with chloroform and remove fat-soluble pigment etc., then with n-butanol extraction, n-butyl alcohol extract is separated by chromatographic process and identifies a kind of novel organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeic acid.Pharmacological evaluation shows, various bacteria is had certain antibacterial activity by this noval chemical compound.
Description
Technical field
The present invention relates to a kind of organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid separating from Cyatheaceae Caulis cyatheae spinulosae platymiscium Caulis cyatheae spinulosae stem and obtaining, Preparation method and use, especially as antibacterial medicine, or the application as antibacterial precursor or lead compound.
Background technology
Caulis cyatheae spinulosae (Alsophilaspinutosa) has survived more than one hundred million year on earth; it it is existing unique woody pteridophyta; also it is pteridophyta the tallest and the biggest in the world; the endangered plants of second class protection it are classified as by country; " living fossil " of research extinct plants and animal and Earth evolution it is called by scientific circles; famous Relict Plant, Caulis cyatheae spinulosae to the formation of species and the research paleontology of floristic region, geologic climate, Paleoenvironmental Evolution research there is important value；It it is the important evidence dividing natural zone.The stem of Caulis cyatheae spinulosae can people's medicine, have wind dispelling to wet, bone and muscle strengthening, the effect such as clearing and antitussive, in Chinese medicine, be referred to as Os Draconis wind.Research shows that the extract of Caulis cyatheae spinulosae stem has antibacterial action.
The present invention is for providing the antibacterial medicine of a kind of structure novel, or as antibacterial precursor or lead compound, has good DEVELOPMENT PROSPECT.
Summary of the invention
It is an object of the invention to provide from Cyatheaceae Caulis cyatheae spinulosae platymiscium Caulis cyatheae spinulosae stem, separate the one obtained novel organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid, Preparation method and use, especially as antibacterial medicine, or the application as antibacterial precursor or lead compound, described organic acid structure is as follows:
The present invention, with alcohol for Extraction solvent, separates with silica gel column chromatography in conjunction with organic solvent extraction and obtains novel organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid.
The flesh and blood of the present invention is only described with example, but present disclosure is not limited to that.
Take dry Caulis cyatheae spinulosae stem, pulverize, leach organic acid with the alcoholic solution of 10%-100%, repeat to extract three times, united extraction liquid, elimination precipitates, then it is concentrated into without alcohol, the organic solvent extraction of the middle or small polarity of use three times, removes fat-soluble pigment etc., then again with taking out organic acid with the immiscible organic solvent extracting of water stratification, then reducing pressure dense obtains organic acids extract.By organic acid through silica gel H short column chromatography, organic solvent { such as chloroform/methanol/water [CHCl in varing proportions respectively3-CH3OH-H2O (7: 1: 0.1 → 2: 1: 0.1)] } for eluting solvent, obtain target compound.
The alcoholic solution of described 10%-100% (w/w) can be methanol, ethanol, glycerol, n-butyl alcohol or their mixture.
The organic solvent extracted except fat-soluble pigment etc. can be petroleum ether, chloroform, dichloromethane, carbon tetrachloride, ethyl acetate, ether or their mixture etc..
Extracting organic acid organic solvent can be n-butyl alcohol or moisture n-butyl alcohol etc..
Eluting organic solvent can be methanol-acetone-aqueous systems, ethanol-acetone-aqueous systems, chloroform-methanol-aqueous systems, chloroform-ethanol-aqueous systems etc..
Novel organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid molecular formula is C17H21O10, white amorphous powder.
Novel organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid can individually or be used in combination with other antibacterials.
Detailed description of the invention:
Below in conjunction with example, the present invention is described in further details, but present disclosure is not limited to that.
Take dry Caulis cyatheae spinulosae stem 1kg, pulverizing, the methanol solution 6000mL room temperature with 80% leaches organic acid, repeats to extract three times, united extraction liquid, elimination precipitates, and is then concentrated into without, after alcohol, extracting three times with chloroform 500mL, remove fat-soluble pigment etc., then again with extracting three times with the immiscible organic solvent n-butyl alcohol 500mL of water stratification, concentration n-butyl alcohol must contain organic acid n-butanol extract, and then concentrating under reduced pressure obtains organic acids extract.By organic acid through silica gel H short column chromatography, organic solvents, chloroform/methanol/water [CHCl in varing proportions respectively3-CH3OH-H2O (7: 1: 0.1 → 2: 1: 0.1)] for elution volume, gradient elution, obtain target compound (3-acetyl-4-O-β-D-glucopyranosidecaffeicacid) 16mg.Novel organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid nuclear magnetic data is as follows: molecular formula is C17H21O10, white amorphous powder.
(400MHzfor1H-NMR, 100MHzfor13C-NMR, CD3OD, δ inppm, JinHz)
Effect experiment:
Experimental strain: golden yellow glucose coccus (Staphylococcusaureus), bacillus subtilis (Bacillussubtilis), escherichia coli (Escherichiacoli) provide by microbial room of Leshan Teachers College.
The mensuration of MIC: from well-grown culture medium, the bacterial aggregate taking 2-3 bacterium colony with asepsis ring joins in 1mL sterilized water, joins in fluid medium standby after mixing.Bacterial concentration is about 1.0 × 105/mL.Taking 96 orifice plates after disinfection by ultraviolet light, every hole adds 190 μ L bacterium solution, and then every hole adds 10 μ L medicinal liquids, sample final concentration respectively 0.125,0.25,0.5,0.75,1.0,1.5,2.0,2.5mg/mL, each concentration makees 3 multiple holes, if the multiple hole of matched group 3, does not add medicinal liquid.37 DEG C of antibacterial cultivates 18-24h, with turbidity for index checking test tube with or without bacterial growth, not show that turbidity, perusal have no the drug level of thalli growth for MIC.
| Escherichia coli | Bacillus subtilis | Gold-coloured staphylococci | |
| MIC | 1.5mg/mL | 1.0mg/mL | 2.0mg/L |
Claims (4)
1. an organic acid 3-acetyl-4-O-β-D-glucopyranosidecaffeicacid, its structure is as follows:
2. organic acid application as claimed in claim 1, it is characterised in that the purposes in preparation antibacterials, antibacterial precursor or lead compound.
3. application according to claim 2, wherein said bacterium is: golden yellow glucose coccus (Staphylococcusaureus), bacillus subtilis (Bacillussubtilis), escherichia coli (Escherichiacoli).
4. comprise the pharmaceutical composition of the organic acid described in claim 1 and pharmaceutically acceptable carrier.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210585946.XA CN103044500B (en) | 2012-12-14 | 2012-12-14 | A kind of organic acid preparation and antibacterial applications |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210585946.XA CN103044500B (en) | 2012-12-14 | 2012-12-14 | A kind of organic acid preparation and antibacterial applications |
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| CN103044500A CN103044500A (en) | 2013-04-17 |
| CN103044500B true CN103044500B (en) | 2016-07-06 |
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| CN201210585946.XA Active CN103044500B (en) | 2012-12-14 | 2012-12-14 | A kind of organic acid preparation and antibacterial applications |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113105471B (en) * | 2021-03-29 | 2022-06-24 | 中国林业科学研究院 | Phenolic acid compound with antioxidant activity and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4610876A (en) * | 1984-09-13 | 1986-09-09 | Canadian Patents & Development Limited | Attractants for fall cankerworm moths |
| JP2004315386A (en) * | 2003-04-14 | 2004-11-11 | Hayashibara Takeshi | Anti-microbial agent |
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2012
- 2012-12-14 CN CN201210585946.XA patent/CN103044500B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4610876A (en) * | 1984-09-13 | 1986-09-09 | Canadian Patents & Development Limited | Attractants for fall cankerworm moths |
| JP2004315386A (en) * | 2003-04-14 | 2004-11-11 | Hayashibara Takeshi | Anti-microbial agent |
Non-Patent Citations (4)
| Title |
|---|
| COMPARISON OF PHENOLIC COMPOUNDS FROM GALLS AND SHOOTS OF PICEA GLAUCA;CHRISTINE KRAUS等;《Phytochemistry》;19971231;59-67 * |
| 孑遗植物桫椤叶化学成分的研究;陈封政等;《西北植物学报》;20081231;1246-1249 * |
| 桫椤叶和茎干抑菌活性初探;弓加文;《安徽农业科学》;20071231;10566-10568 * |
| 桫椤茎杆中化合物成分研究;成英等;《安徽农业科学》;20111231;18672-18674 * |
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Effective date of registration: 20180515 Address after: 610000 Sichuan Chengdu high tech Zone Shengan Street 401, 1 Building 2 unit 16 level 1608. Patentee after: Chengdu Ge pure biological medicine Co., Ltd. Address before: 614000 Leshan Normal University, 778 Binhe Road, Shizhong District, Leshan, Sichuan Patentee before: Leshan Teachers College |
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